57780-74-2Relevant academic research and scientific papers
PPh3/Selectfluor-Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis
Yang, Zhen,Chen, Siwei,Yang, Fang,Zhang, Chenxi,Dou, You,Zhou, Qiuju,Yan, Yizhe,Tang, Lin
, p. 5998 - 6002 (2019/08/21)
By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols.
Resolution of pentafluorophenyl 2-phenylpropanoate using combinations of quasi-enantiomeric oxazolidin-2-ones
Shaye, Najla Al,Benoit, David M.,Chavda, Sameer,Coulbeck, Elliot,Dingjan, Marco,Eames, Jason,Yohannes, Yonas
experimental part, p. 413 - 438 (2011/06/17)
The kinetic, mutual and parallel resolution of a series of structurally related active esters derived from 2-phenylpropanoic acid using a combination of quasi-enantiomeric oxazolidin-2-ones is discussed.
Scandium triflate-catalyzed intramolecular Friedel-Crafts acylation with Meldrum's acids: insight into the mechanism
Fillion, Eric,Fishlock, Dan
scheme or table, p. 6682 - 6695 (2011/02/26)
The intramolecular Friedel-Crafts acylation of arenes with Meldrum's acid derivatives catalyzed by Sc(OTf)3 was reported as a mild and general entry into functionalized 1-indanones. Mechanistic investigations were undertaken to determine the rate-determining step in the acylation sequence using Meldrum's acid, as well as to examine the role of the Lewis acid catalyst. Enolizable Meldrum's acid derivatives react via an acyl ketene intermediate under thermal conditions, while quaternized Meldrum's acid derivatives are thermally stable and only act as effective Friedel-Crafts acylating agents in the presence of a Lewis acid catalyst. The acylation was postulated to proceed through direct acylation of a Lewis acid-activated carbonyl. In the catalytic Friedel-Crafts acylation of Meldrum's acids, triflic acid appeared to be the active catalytic species, with Sc(OTf)3 serving as a very mild and convenient reagent for its delivery.
A method for determining the enantiomeric purity of profens
Coulbeck, Elliot,Eames, Jason
body text, p. 635 - 640 (2009/08/15)
A simple method for determining the enantiomeric purity of profens (based on the carbon skeleton of 2-phenylpropionic acid) is discussed. The enantiomeric purity of a given profen can be determined by stereospecific DCC self-coupling to give a statistical diastereoisomeric mixture of racemic and meso- anhydrides. The relative ratio of diastereoisomers formed can be related to the enantiomeric excess of the original carboxylic acid.
Homobenzotetramisole-catalyzed kinetic resolution of α-Aryl-, α-Aryloxy-, and α-Arylthioalkanoic acids
Yang, Xing,Birman, Vladimir B.
supporting information; experimental part, p. 2301 - 2304 (2010/01/19)
Effective kinetic resolutions of α-aryl-, αaryloxy-, and α-arylthioalkanoic acids have been achieved via in situ generation of their symmetrical anhydrides and enantioselective alcoholysis in the presence of homobenzotetramisole (HBTM) 3.
Parallel kinetic resolution of racemic 1-phenylethanol using quasi-enantiomeric combinations of carboxylic acids mediated by N,N′-dicyclohexylcarbodiimide and 3,5-lutidine
Shaye, Najla Al,Boa, Andrew N.,Coulbeck, Elliot,Eames, Jason
, p. 4661 - 4665 (2008/12/20)
The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric 2-arylpropionic and butanoic acids mediated by a N,N′-dicyclohexylcarbodiimide (DCC)/3,5-lutidine coupling is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield.
